Soulgoober,
Samujohn is correct, in my opinion, about starting with the amp over the digital front end (if you have to choose the biggest impact). I would have to disagree on his point of going with a power amp and adding a 'shack volume control.
I am of the opinion that amps of 6-8 years of age vary little from the most current amps (changes in this arena have been much, much more gradual than the digital front end changes). The better the power supply the better off you are (IMO).
It would not be a bad idea to consider a used integrated amplifier as well. Unless you listen to radio, I would avoid the receiver route. Is Outlaw really that great? Personally, I would suggest not. Perhaps comparing it to the Technics it will be a good improvement, but I think you can get much farther along without any more money (possibly even less). The Outlaw stuff is good when comparing it to new stuff and considering the "features" you get. Sound quality is fine, just not as good as you can get used for less money.
If I understand correctly, your budget is increased to $1500 for both pieces of equipment. You should be able to arrive at very good used equipment within this budget. Be careful about buying used CD players, unlike the amps they have seen much improvement in recent years and also unlike the amps, they wear out. While I have never had a toe job, this whole concept is intriguing to me (ha ha). I have also read positive comments on these units. My suggestion would be to do a litte more research on good used integrated amps and then come up with a short list of both amps and acceptable CD players. Buy the best deal that comes up first, regardless of which component it is.
This will give you a chance to determine yourself what you like and don't like about the sound of the new equipment. Based on this, you can then adjust your demands for the remaining piece of equipment. For example if you get the amp first and find it is a bit brighter than you are seeking, you can adjust the CDP accordingly (or obviously other sound issues you want to adjust for).
There are many good used CDP in the $500-$800 range that can work here. I think looking at the price breakdowns of different CDPs may be a good move here. What level of equipment can you get within your budget for each of the two items. In my opinion, you need to really spend a lot of money to get a phenomal CDP (well beyond your budget) and there is a big difference between a phenom. CDP and a good CDP (you are likely to be looking at a good CDP). To get the most out of a truly great CDP you need very, very good components everyplace else. This is not going to happen at this budget.
At your budget, you can get a very satisfying rig together and in a couple of years look to upgrade you speakers. Perhaps you should consider what are the most important sonic characteristics you are seeking. At these price points, there will be sonic characteristics (which is not necessarily bad, just should be thought out). Also, keep in mind your speaker's sound.